(4-BroMo-2-propoxyphenyl)Methanol synthesis

Yield:1094510-28-7 99%

Reaction Conditions:

with methanol;sodium tetrahydroborate at 20;

Steps:

25

Intermediate 25: [4-bromo-2-(propyloxy)phenyl]methanol; To a solution of 4-bromo-2-(propyloxy)benzaldehyde, intermediate 24, (8.4 g, 34.6 mmol) in methanol (100 mL) was added portionwise sodium borohydride (1.444 g, 38.0 mmol) and the reaction mixture was stirred at room temperature for 30 minutes and then poured into water.After extraction with dichloromethane, the organic phase was dried over sodium sulfate and concentrated under reduced pressure. The title product, [4-bromo-2-(propyloxy)phenyl]methanol was obtained as a pale yellow oil (8.35 g, 34.1 mmol, 99 %). LCMS: Rt= 3.06 min., no mass found. ¹H NMR (CDCI₃) ￡7.05 (dd, 1 H), 6.95 (dd, 1 H), 6.9 (s, 1 H), 4.6 (d, 2H), 3.9 (t, 2H), 2.2 (t,1 H), 1.75 (m, 2H), 1.05 (t, 3H).

References:

WO2010/15652,2010,A2 Location in patent:Page/Page column 41